


Mistress May I?

by KittyinShadows



Category: Batman - All Media Types
Genre: BDWW 2020, Bottom Damian Wayne, Crossdressing, Dirty Talk, Exhibitionism, Grinding, Light Dom/sub, M/M, Oral Sex, Undercover, gender play?? is that a thing??, no beta we die like robin, they are seen in the act
Language: English
Status: Completed
Published: 2020-11-01
Updated: 2020-11-01
Packaged: 2021-03-08 23:01:54
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,724
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27324700
Author URL: https://archiveofourown.org/users/KittyinShadows/pseuds/KittyinShadows
Summary: Damian and Tim had been planning this bust for weeks.There was only one problem. The club was having an unannounced ‘ladies night’.Tim’s voice came through his comm. “Tell him your girlfriend is on her way and can you wait there until she gets here.”He wasn't expecting Caroline Hill.For day 1 of Bottom Damian Wayne Week, prompt: Undercover
Relationships: Tim Drake/Damian Wayne
Comments: 4
Kudos: 159





	Mistress May I?

**Author's Note:**

> ok Im 4 hours late in my time zone but here it is. Written in an hour and completely unedited. enjoy <3

Damian and Tim had been planning this bust for weeks. Damian would go undercover as a clubgoer and plant as many bugs as he could, and gather as much information from the backroom meeting going on that night. Tim would be costumed several roofs away, collecting the data Damian sent and on standby if he was needed. There was only one problem.

The club was having an unannounced ‘ladies night’.

When Damian reached the front of the line, the slab of man the club called a bouncer immediately placed his hand on his chest, and said “Nope.”

“Ex _cuse_ me?”

The man gestured to a piece of paper taped on the door that read “Ladies night.”

“No guys in unless they got a lady with ‘em.”

“Wha—that’s not even what ladies night means!”

The bouncer shrugged. “Is here.”

“Are you—that’s—” He was about to drop a ‘Do you know who I am?’ when Tim’s voice came through his comm.

“Tell him your girlfriend is on her way and can you wait there until she gets here.” He must have called Steph or Cass in. Ugh. Someone who didn’t know any details of the case was just what he needed. But this had to be done today, so he would simply have to deal.

“My girlfriend will be here shortly. May I wait over here?” He gestured at the wall near the entrance.

“Depends. Is she hot?” Oh this man was lucky he didn’t kill anymore.

He forced a smarmy grin onto his face. “Very.”

“Heh. Alright.” Asshole. He moved to lean against the wall a couple yards away. Then, reluctantly, he pulled out his least favorite prop for the job: a vape without nicotine, just an obnoxious cinnamon scent. Leaning with one foot against the wall, dressed in tight black jeans and a tighter black shirt, clouds of vapor puffing from his lips, he had to admit he looked quite the part, much as he loathed it. He couldn’t help picking up conversations as he waited. Hopefully he would hear something important. People—mostly women, he noted—chattered excitedly. Some sounded excited for the drugs they’d find inside, others for the hookups, others just for the fun. The bouncer was at least more respectable speaking to women than about them. 

After eight minutes a woman’s voice called, “Babe, over here!” He didn’t pay it mind, just another new arrival to the line. He still watched, as he had been watching everything, as the woman approached the club in the fast little footsteps of someone in too tall heels. It...almost seemed like she was waving at him? “Babe! It’s me!” Oh fuck she was waving at him. Caucasian, long brown hair, form fitting red halter dress—he didn’t know this lady. She continued to approach. He lowered the vape and started to shake his head.

“I think you’ve got me confu—oomph!” He was being kissed. Just a peck, but he still snapped his mouth shut. Her arms wrapped around his neck, her breasts pressed against his chest—that’s a new sensation.

In his ear she spoke, suddenly deeper and horrifyingly familiar. “Red Robin to the rescue. Damian, meet Caroline Hill.”

He made himself smile brightly. His cheeks resented it. “Did you do something with your hair? I almost didn’t recognize you.” 

Tim ran his fingers through the long strands of hair, smiled with lips painted deep scarlet. “You noticed! Come on, I’m so excited to check this place out! Do you think they know that one drink I like?”

He slipped his arm around Tim’s shoulders and walked them towards the door. “Maybe. We’ll see.” He handed the expectant bouncer a $5 bill as he waved them in. Instantly they were hit with too loud bass and swarms of people. They made their way to the bar, where Tim ordered a Red Bull he made Damian pay for. While Tim sipped, they surveyed the room, accounting for how many people, noting familiar faces, how many guards there were and where. When no one was looking Damian stuck a bug to the bottom of the other side of the bar. Then, unfortunately, it was time for what would be most of the night: dancing. 

They joined the mass near the bar; the plan was to migrate around the dance floor over time, to keep an eye on everything. Damian didn’t enjoy dancing. It wasn’t that he _couldn’t_ dance. Between Talia and Bruce he’d been taught the traditional dances of a dozen cultures. It was just this monotonous bounce-jump-wave-arms-rock-hips sort of dance that didn’t suit him. It did seem to suit Tim, though. His long, muscled legs were bare, shadows and flashing lights showing every detail. The dress hugged his hips that swayed so suggestively. Equally strong, bare arms were held above his head. His long, graceful fingers occasionally ran through thick shiny hair. His pretty red lips occasionally moved along to the lyrics. When their eyes met under the dim lights, Damian felt a shiver run down his spine. 

It wasn’t fair how pretty Tim was. He couldn’t have taken more than five minutes to become Caroline, yet here he was looking ravishing and perfect. At several points men tried to sidle up to ‘Caroline’, but every time they were politely refused, with a gesture to Damian. The next time a man approached, Damian pulled Tim back against him with a glare. And then they were dancing _together_ , movements synced, with Damian’s hands on Tim’s waist or hips, and Tim’s arms reaching behind Damian's neck. They weren’t grinding, exactly. Just dancing...closely. Every brush of his bulge against Tim’s ass reminded him that he wasn’t wearing a cup. Half his focus went to not reacting, which, funnily enough, just made him think about the friction more. 

When the meeting was maybe half an hour off, Tim turned in his arms and pressed their bodies flush, hips tight and fake breasts squished between them. Swaying together, he could feel the flexing of Tim’s abs. Right into his ear Tim spoke, the sound getting doubled by the comm in his other ear. “I’ll bet a horny couple would be able to get into that room.” Over Tim’s shoulder, he could see a guard standing at a blank door beside the restrooms. They knew from the blueprints there were several rooms back there, probably used for hookups quite often. Likely there were instructions to not let anyone back while the meeting was on, but money talks. _Then_ they were grinding. Tim moved Damian’s hands to his ass, and their swaying became punctuated with rutting. One particularly good grind had Damian seeing stars as he realized that Tim was half hard too. Fuck. This was not in the plan. But there was no going back now. Tim started nipping at his neck, sucking a mark into his skin. So Damian moved to return the favor, licking along the shell of Tim’s ear, and tugging on the lobe. Tim shivered in his arms, hips moving faster in his hands. Then their lips met, sloppy and wet and open-mouthed, teeth pulling on lips and tongues dancing together and lips getting deliciously swollen. 

Lips suddenly bereft, he found himself being tugged along to the door as fast as Tim’s little heels could go. In front of the guard, Tim begged in a breathy, desperate voice that was only somewhat fake, “Pl _ease_ tell me there’s a place a girl can get some privacy around here?”

The guard smirked a little. “There is, but not tonight. Sorry ma’am, but we got a private party goin on.”

Tim let out a whine that was a lot more fake. “Come on, the whole place? Not even a closet? We can pay!” And then Tim reached into Damian’s pocket for his wallet, pulling out a very large bill while clearly flashing the many other very large bills inside. The guards' eyes went from the wallet to Damian’s face. He felt the moment he was recognized. The guard took the bill and opened the door, guiding them to the first door on the right, which opened to show a small room with a long couch covered with stains. As soon as they were in Tim recaptured his lips. He heard the door click shut behind them, cutting off the guard's low chuckle. They separated once they couldn't hear him anymore. Damian quickly planted another bug, while Tim pulled his phone from his bra and consulted the blueprints. 

“There’s another room between us and the meeting. We’ll have to get closer once it starts. Luckily, they don’t appear to have a camera in the hall. Still, I should be the one to go plant the next device just in case. Since I’m in costume.”

Damian nodded in agreement, and settled onto the awful couch for a long and uncomfortable wait.

“What are you doing?” Tim questioned, brows crooked in confusion. 

“What?”

“Aren’t we gonna,” Tim gestured between their bodies.

Damian felt his already flushed face heat even more. “It. It wasn’t just for show?” 

“I mean,” Tim’s shoulders scrunched up a little, like he was apprehensive. He glanced away for a long second before meeting Damian’s eyes, desire plain on his face. “I can’t exactly go back out there like this. Bit _hard_ to tuck if you catch my meaning.” And sure enough when he looked Tim’s skirt had a plain bulge. A quite...significant bulge. 

“That...does look uncomfortable,” he hedged.

“Yeah.” Tim stalked closer. “Yours too. Maybe we could help each other out.”

“That. I would be amenable.” 

“ _Great_.” Then Tim was on his lap, shoving his tongue into his mouth. 

“Mmmmph.”

Tim leaned back as he ground down, making an exaggerated high moan as he grinned. “Aaaaah~ Yes! Damian!” Damian tried to put his hands on Tim’s hips, but the other man slapped them away with a low, “I don’t think so Dami. You’ll be doing as I tell you.” Damian shuddered, cock jumping in its confines. “Ohhh, like that do we? Hm? Do you like that everyone thinks you’re in here getting some when actually your little _girlfriend_ is working you over?”

He gasped, unable to hold the shaky moan in his throat. 

“Oh you _do_. Good little slut, I’ll use you so nice tonight.” Tim got off his lap, moving to lay back on the couch facing the door, legs spread obscenely in his tight red dress. Up his skirt Damian could see his cock, thick underneath a pair of panties. Fuck. “Now you’re going to suck me off, and if you’re really good I’ll let you get off fucking the couch during. Sound good?”

“Hh. Yes.”

“Yes what?”

“Yes _please_.”

“Hm. I was actually going for Mistress, but I guess that’ll do.”

Damian couldn’t help the way his hips jumped. It seemed to please his partner, though, and Tim pulled those panties down until they hung off one lifted ankle. His dirty smile served as invitation enough. Damian dived in. Carefully shoving the skirt up just enough to get at his goal, he delicately took the tip into his mouth. Shoved beneath Tim’s skirt, cock pushing his jaw wide, Damian was suddenly much more intimidated. But then a bead of precum leaked onto his tongue, salty and musky and good, and Tim let out a pleased, “Hhhmmmm,” and Damian was instantly hungry for more. So he let the hand in his hair push him further, and he let Tim’s leg come up to rest on his back, panty dangling from his ankle. He closed his eyes, just enjoying the scent and taste and sensation.

Tim kept making those fake high “Ah~ Ah~” noises, but they were interspersed with low comments. “Just like that babybat, suck me down.” “That’s my good boy, taking me so well.” “Just a little further and you’ll have it all, I know you want it, come on slut.” “Look how desperate you are, humping the cushions like a good little whore.” He didn’t even realize he was doing it until Tim said. Then all of a sudden he was desperate to be out of his tight pants, scrabbling at the zipper and yanking his dick out. 

Tim yanked his hand back to him. “I don’t think so. No touching until I say so.”

So he sucked harder, intent on pleasing his partner enough to be rewarded.

After several long minutes they both heard voices over their own sounds. Tim cranked his breathy volume up in response. “Ah! Yes, yes, right there, so good so gooood~”

“Marco what the fuck did I tell you?” a displeased man demanded in the hallway, presumably to the guard.

“Nobody back here till after yer done with the place. I know, boss, but this guy had cash. Chick took a hundred bucks from his wallet like it was nothin’. He didn’t even blink. ‘Sides, they seem pretty busy.”

“I don’t pay you to roll over for every guy with some money to blow!”

The guard lowered his voice to something conspiratorial. Damian listened carefully, pausing his sucking.

"Boss, I think that's Bruce Wayne's boy in there."

"No shit. Which one? Richard? He hasn't been on the club scene in years."

"No, the youngest one. That punched all those reporters when he first showed up?”

“Damian? Fuck, if he came around more that’d be damn good for business.”

There was a very subtle click of the door opening. Damian forced himself not to tense, to keep fucking the couch and making Tim moan. They lowered their voices, but Damian was trained in listening, and heard every word.

“Ho-ly-shit. I never would’ve stuck Brucie’s brat for a giver. Guess that’s how they get all those ladies huh?” Under his hand Tim shook.

“Hh—ah! Hh. L-love your mou-th-th Damiannnn!” Fucker was laughing at him! He tightened his jaws enough his teeth grazed the cock in his mouth, an overt threat. Tim just yanked his hair and he got caught in a moan. Fuck.

“Yeah, somehow I think it’s the money and fancy clothes, not his generosity,” another voice spoke up. “Now can we get fuckin to it? Time’s money.”

The door clicked shut again, and the voices moved down the hall, laughing about rich kids and their loose tongues, hah hah _hah_. 

Tim’s voice dropped again. “Did you hear that babybat? Even they’re impressed with your whore mouth.”

“Mmmph. Ggg.” Talking back didn’t seem to work with his mouth full. 

“Good boy. Choke on me. Now touch yourself, and get ready to swallow my cum.”

He quickly put a hand around himself and jerked into it, as he swallowed Tim’s perfect cock as deep as he could and moaned around it. He stopped bobbing, instead letting Tim fuck hard into his mouth. When Tim came he could barely taste it, hot liquid pumping onto the very back of his tongue and throat. Before he could choke he swallowed, panting fast through his nose, head dizzy as he desperately fucked his hand to orgasm. 

Barely a second after pulling off Tim’s cock and the man was tucking himself away, grabbing a recording device from Damian’s pocket and exiting the room. Once the endorphins passed he put himself back together and used the tissues sitting beside the couch to wipe his cum from the couch. Jesus. His first time with Tim and all that’s left of it was yet another stain on an ancient sofa. By the time he was ready to go Tim was back. He looked...fucked out. The lipstick was smeared a little, his long wig was disheveled, the dress wrinkled...He looked good.

Fuck.

“All set. Let’s get out of here.” They hurried out, past the smirking guard, through the pulsing crowd, and out into the cool night. As they walked arm in arm, Tim’s smeared lips quirked almost nervously. “Let’s get through that recording and figure out our next step. And then...I think I owe you something more sustancial.”

Damian swore his stomach flipped over, then. He could get on board with that…

—·—

The next morning he and Caroline were splashed on the front page of the Gotham Daily, on their way out from the club. The headline read: “The Apple Doesn’t Fall Far From the Tree: Damian Wayne spotted out on the town with unknown hookup!”

...Oops.


End file.
